(R)-2-Benzyloxycarbonylamino-3-methyl-butyric acid tert-butyl ester | 65464-61-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R)-2-Benzyloxycarbonylamino-3-methyl-butyric acid tert-butyl ester
• 英文别名: tert-butyl (2R)-3-methyl-2-(phenylmethoxycarbonylamino)butanoate
• CAS: 65464-61-1
• 化学式: C₁₇H₂₅NO₄
• 分子量: 307.39
• InChiKey: YRHPJONYYIHCIG-CQSZACIVSA-N

物化性质

• 沸点：
  418.8±38.0 °C(Predicted)
• 密度：
  1.069±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-2-Benzyloxycarbonylamino-3-methyl-butyric acid tert-butyl ester 在 10% palladium on activated carbon 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 D-valine t-butyl ester
  参考文献：
  名称：

  A Bismuth(III)-Catalyzed Friedel−Crafts Cyclization and Stereocontrolled Organocatalytic Approach to (−)-Platensimycin

  摘要：

  A high yielding route to the (-)-platensimycin core is communicated. This entailed the discovery of Bi(OTf)(3) to catalyze a Friedel-Crafts cyclization of a free lactol, supplemented by LiClO4 to suppress the Lewis basicity of the sulfonate group. After TBAF-promotecl cyclodearomatization, a diastereoselective conjugate reduction of a dienone was achieved by adopting amine-based organocatalytic rationales to reverse the inherent steric control of the substrate.

  DOI：

  10.1021/ol102390t
• 作为产物：
  描述：

  D-缬氨酸 、 氯甲酸苄酯 在 硫酸 、 sodium carbonate 、 magnesium sulfate 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 25.0h， 生成 (R)-2-Benzyloxycarbonylamino-3-methyl-butyric acid tert-butyl ester
  参考文献：
  名称：

  A Bismuth(III)-Catalyzed Friedel−Crafts Cyclization and Stereocontrolled Organocatalytic Approach to (−)-Platensimycin

  摘要：

  A high yielding route to the (-)-platensimycin core is communicated. This entailed the discovery of Bi(OTf)(3) to catalyze a Friedel-Crafts cyclization of a free lactol, supplemented by LiClO4 to suppress the Lewis basicity of the sulfonate group. After TBAF-promotecl cyclodearomatization, a diastereoselective conjugate reduction of a dienone was achieved by adopting amine-based organocatalytic rationales to reverse the inherent steric control of the substrate.

  DOI：

  10.1021/ol102390t

文献信息

• A Bismuth(III)-Catalyzed Friedel−Crafts Cyclization and Stereocontrolled Organocatalytic Approach to (−)-Platensimycin
  作者：Stanley T.-C. Eey、Martin J. Lear

  DOI：10.1021/ol102390t

  日期：2010.12.3

  A high yielding route to the (-)-platensimycin core is communicated. This entailed the discovery of Bi(OTf)(3) to catalyze a Friedel-Crafts cyclization of a free lactol, supplemented by LiClO4 to suppress the Lewis basicity of the sulfonate group. After TBAF-promotecl cyclodearomatization, a diastereoselective conjugate reduction of a dienone was achieved by adopting amine-based organocatalytic rationales to reverse the inherent steric control of the substrate.